Motorola’s Q phone weighs 4.1 ounces, fits easily in a shirt pocket, and is just 11.5 millimeters thick. It looks like a cross between Motorola’s successful Razr flip phone and Palm’s blockbuster Treo smart phone, and it’s tempting to compare the Q to the Treo 700p and Research in Motion’s BlackBerry 7290; all three devices are designed to let you check your e-mail, make telephone calls, save contacts in an address book, update your calendar, and browse the Web.

But Motorola isn’t positioning the Q as a Treo killer. Mike Booth, a senior director at Motorola who oversaw the product’s management, told me that it isn’t just another smart phone for business executives. Its relatively low price, thinness, stereo speakers, and 1.3-megapixel camera make it ideal for people who don’t have high-power jobs but would like to be more organized–people like artists, college students, and stay-at-home parents.

Most cell phones now have calendars and address books built in, but they also have interfaces that must have been designed by engineers who majored in torture–“Death by a thousand clicks!” In contrast, the Q’s Qwerty keyboard, jog dial, and five-way cursor control make its advanced features relatively straightforward to use–especially text messaging and the built-in Web browser.

The Q started as a project to make a stylish smart phone: think of an ultrathin Razr with a Qwerty keyboard. Motorola wanted something that execu­tives could use for both voice and data during the week and then take home for weekends with their fami­lies. But after trials that involved hundreds of ­people inside Motorola–many of whom were not technologists but receptionists, drivers, factory workers, and so on–the company realized that it had created something else altogether: an intelligent device that, says Booth, could be used by the “technologically illiterate.”

For just this reason, explains Booth, ­Motorola decided that the Q should run the Windows Mobile 5 operating system. After all, what could possibly be more familiar than Windows?

I disagree with that reasoning. In my tests I found Windows Mobile 5 on the Q to be slow, buggy, and cumbersome. Worst of all, the phone’s software generally fails to take into account the user’s current activities and goals–what you might think of as the “context.” Instead, Windows Mobile forces the user to understand what’s going on inside the phone–how data and functionality are divided among the phone’s various applications, how menus are structured, and even where files are stored.

In other words, the Q succeeds in bringing the experience of Windows to the mobile phone. This is its failing.